2,4,6-tricyclohexyl-[1,3,5]trioxane | 6556-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧烷
• 英文名称: 2,4,6-tricyclohexyl-[1,3,5]trioxane
• 英文别名: 2,4,6-tricyclohexyl-1,3,5-trioxane；trimer of cyclohexane carbaldehyde；2,4,6-Tricyclohexyl-[1,3,5]trioxan；2,4,6-Tricyclohexyl-<1,3,5>trioxan；2,4,6-Tricyclohexyl-(1,3,5)-trioxan；2,4,6-Tricyclohexyl-1,3,5-trioxan
• CAS: 6556-71-4
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: MVDCFRCBNYLINX-UHFFFAOYSA-N

物化性质

• 沸点：
  430.6±25.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6-tricyclohexyl-[1,3,5]trioxane 在 碘代三甲硅烷 、 lithium perchlorate 、 (-)-menthol trimethylsilyl ether 、 三氟乙酸 、 sodium iodide 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 (S)-cyclohexyl(1-(hydroxymethyl)cyclohexyl)methanol
  参考文献：
  名称：

  Acid-catalyzed aldol-Meerwein–Ponndorf–Verley-etherification reactions—access to defined configured quaternary stereogenic centers

  摘要：

  A novel asymmetric aldol-reduction-etherification process of aliphatic enolizable aldehydes is described. The intermediately formed aldol adducts-beta-hydroxyaldehydes-were reduced and transformed into the corresponding 1,3-diol ethers by external secondary alcohols at the same time. Thus, with the help of chiral secondary alcohols an access to optically active 1,3-diol ether is given. Furthermore, asymmetric cross-aldol-Meerwein-Ponndorf reactions of enolizable aldehydes can also be realized under these reaction conditions. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.069
• 作为产物：
  描述：

  环己烷基甲醛 在 乙酰甲基三苯基溴化鏻 作用下， 反应 24.0h， 以76%的产率得到2,4,6-tricyclohexyl-[1,3,5]trioxane
  参考文献：
  名称：

  乙酰基三苯基溴化organic在有机合成中的应用：醛环三聚的有用催化剂

  摘要：

  乙酰基三苯基溴化phosph（ATPB）是在无溶剂条件下脂族醛环三聚的有用催化剂。与多种官能团（例如烯烃，醚，酯，溴化物，叠氮化物和二酯）束缚的醛也可以在ATPB的催化下进行环三聚。

  DOI：

  10.1016/s0040-4020(01)00588-9

文献信息

• Acetonyltriphenylphosphonium bromide in organic synthesis: a useful catalyst in the cyclotrimerization of aldehydes
  作者：Yung-Son Hon、Chia-Fu Lee

  DOI：10.1016/s0040-4020(01)00588-9

  日期：2001.7

  Acetonyltriphenylphosphonium bromide (ATPB) is a useful catalyst for the cyclotrimerization of the aliphatic aldehydes under solvent-free condition. The aldehydes tethered with a variety of functionality such as olefin, ether, ester, bromide, azide and diester could also be cyclotrimerized under the catalysis of ATPB.

  乙酰基三苯基溴化phosph（ATPB）是在无溶剂条件下脂族醛环三聚的有用催化剂。与多种官能团（例如烯烃，醚，酯，溴化物，叠氮化物和二酯）束缚的醛也可以在ATPB的催化下进行环三聚。
• Antimony(<scp>v</scp>) cations for the selective catalytic transformation of aldehydes into symmetric ethers, α,β-unsaturated aldehydes, and 1,3,5-trioxanes
  作者：Renzo Arias Ugarte、Deepa Devarajan、Ryan M. Mushinski、Todd W. Hudnall

  DOI：10.1039/c6dt02121b

  日期：——

  acidity of [2][OTf] was exploited in the catalytic reductive coupling of a variety of aldehydes into symmetric ethers of type L in good to excellent yields under mild conditions using Et3SiH as the reductant. Additionally, [2][OTf] was found to selectively catalyze the Aldol condensation reaction to afford α-β unsaturated aldehydes (M) when aldehydes with 2 α-hydrogen atoms were used. Finally, [2][OTf]

  通过用二溴三苯基苯乙烯硼烷处理1-lithio-8-diphenylphosphinonaphthalene，然后用AgOTf提取卤化物，以优异的收率制备了1-triphenylphosphinonaphthyl -8-triphenylstibonium triflate（[ 2 ] [OTf]）。发现该锑（V）阳离子对氧气和水稳定，并表现出出众的路易斯酸度。[ 2 ] [OTf]的路易斯酸度是在Et 3 SiH作为还原剂的条件下，在温和的条件下，以良好至极佳的收率，将多种醛催化还原偶联为L型对称醚。此外，发现[ 2 ] [OTf]选择性催化Aldol缩合反应，得到α-β不饱和醛（M）当使用具有2个α-氢原子的醛时。最后，[ 2 ] [OTf]催化脂肪族和芳香族醛的环三聚反应，以高收率和高选择性提供了工业上有用的1,3,5三恶烷（N）。这种膦-sti基序是同类催化系统中的第一种，它能够以
• Stereoselective one-pot synthesis of highly differently substituted thiochromans
  作者：Andrea Seifert、Rainer Mahrwald

  DOI：10.1016/j.tetlet.2009.09.009

  日期：2009.11

  A highly stereoselective one-pot procedure to anti-configured thiochromans is described. This reaction functions at room temperature in the presence of catalytic amounts of trifluoroacetic acid. The transformation gives a selective but optional access to highly substituted thiochromans, which have been not attainable until now.

  描述了一种高度立体选择性的一锅法，用于反构硫硫氰酸酯。该反应在室温下在催化量的三氟乙酸存在下起作用。通过这种转化，可以选择性地但可选地获得高度取代的硫代色团，而这是目前为止无法实现的。
• A High Yield Procedure for the Me3SiNTf2-Induced Carbon-Carbon Bond-Forming Reactions of Silyl Nucleophiles with Carbonyl Compounds: The Importance of Addition Order and Solvent Effects
  作者：Kazuaki Ishihara、Yukihiro Hiraiwa、Hisashi Yamamoto

  DOI：10.1055/s-2001-18761

  日期：——

  We demonstrate the efficiency of Me3SiNTf2 (0.3-1.0 mol%) as a strong Lewis acid catalyst for the Mukaiyama aldol and Sakurai-Hosomi allylation reactions, and that the slow addition of carbonyl compounds to a solution of acid catalyst and Me3Si-Nu is very important for suppressing side products; this may be widely accepted as a common and reasonable general procedure for the Lewis acid-induced reaction of Me3Si-Nu with carbonyl compounds.

  我们证明了 Me3SiNTf2 (0.3-1.0 mol%) 作为 Mukaiyama 醇醛和 Sakurai-Hosomi 烯丙基化反应的强路易斯酸催化剂的效率，并且将羰基化合物缓慢添加到酸催化剂和 Me3Si-Nu 的溶液中非常有效。对于抑制副产物很重要；这可能被广泛认为是 Me3Si-Nu 与羰基化合物路易斯酸诱导反应的常见且合理的通用程序。
• Hydroformylation of cyclohexene catalysed by homogeneous bimetallic systems
  作者：Masanobu Hidai、Atsushi Fukuoka、Yokio Koyasu、Yasuzo Uchida

  DOI：10.1039/c39840000516

  日期：——

  Homogeneous bimetallic systems such as Co2(CO)8–Ru3(CO)12 and [Et4N][FeCo3(CO)12] show high catalytic activity for the hydroformylation of cyclohexene compared with Co2(CO)8 alone.

  同质双金属系统，如Co 2（CO）8 -Ru 3（CO）12和[等4 N] [FeCo系3（CO）12 ]示出了用于用Co相比环己烯的加氢甲酰化催化活性高2（CO）8单独。